There are two ways of looking at Masaoka Shiki (1869-1902):
Viewed historically, Shiki was the first “haiku” writer. So “haiku” really began only with Shiki, near the end of the 19th century. Everything before him was hokku, in the wider context of haikai.
Viewed technically, however, Shiki was the last of the prominent writers of hokku; Shiki’s verse still followed the old hokku requirements of season and of length of phonetic units, and in fact most of them are indistinguishable in form and content from hokku. Their peculiarities are due to Shiki’s own view of what verse should be, but that view in practice was still so conservative that if Shiki had been both the first and the last “haiku” writer, his verses would still be considered hokku, if sometimes a bit odd or flat.
Numbers of Shiki’s verses were negatively influenced by his chronic illness. One feels on reading them that not only was the man sick, but those particular verses are sick as well. Nonetheless, R. H. Blyth was able to say that even though Shiki’s personality is unattractive, “we are struck with the large number of excellent, perfect verses which he wrote.” When he was good he was pleasantly good, and when he was bad, his verses seem ill or flat and two-dimensional.
From Shiki onward, the “haiku” he began went downhill. So we can regard Shiki as either the last major writer of the hokku, or as the first writer of the haiku. If seen as the latter, we must recognize that Shiki has little or nothing in common with what is called modern haiku in the West today. Conservative modern Japanese haiku (which is still, for the time being, the preferred kind in Japan), is more closely related to Shiki through his student Kyōshi, whose verses were not as good on the whole as those of his teacher.
Blyth attributes Shiki’s failures and weaknesses to the fact that Shiki had no religion, that consequently we feel in him “some want of depth; the baby has been thrown out with the bath-water.” There is indeed something very superficial in Shiki, and Blyth said correctly that “we feel something a little hard, superficial, unloving in him.”
As unattractive a personality as he may have been, quite a few of his hokku are tranquil and pleasant, and as readers here know, I often compare his better verses to the pleasant block prints of Kawase Hasui (1883-1957) and Hiroshi Yoshida (1876-1950). If you are not familiar with their work, find some examples on the internet, and you will easily see the parallels with the verses of Shiki.
As an example of Shiki at his best, Blyth gives this verse (my translation here), which differs not one whit from earlier hokku:
Shima-jima ni hi wo tomoshikeri haru no umi
Island-island at light wo have-been-lit spring ‘s sea
On all the islands,
Lamps have been lit;
The spring sea.
This is an interesting mixture of elements, all having to do with spring and the increasing Yang energy that grows out of Yin. We see that in the overall subject of the verse (spring) and in the lighting of the lamps in the mild darkness. We see the shadowy islands in the evening sea, and the lights twinkling here and there upon them, near and far.
If all Shiki’s verses had been like this, we would perhaps see him differently.